148679-64-5Relevant articles and documents
A new regioselective synthesis of isopavine and pavine alkaloids via double cyclization of N-(1,2-diarylethyl)-N-(2-phenylsulfinylethyl)formamide
Shinohara, Tatsumi,Takeda, Akira,Toda, Jun,Sano, Takehiro
, p. 981 - 992 (2007/10/03)
Pummerer reaction of N-[1,2-(3,4-dimethoxyphenyl)ethyl]-N-(2-phenylsulfinylethyl)formamide (9) using trifluoroacetic anhydride and boron trifluoride etherate caused double cyclization to give N-formylisopavine (21). Acid catalyzed cyclization of the 1,2-dihydroisoquinoline (23) prepared from 4-phenylthio-1,2,3,4-tetrahydroisoquinoline (11) gave N-formylpavine (26). LiAlH4 reduction of the N-formates (21 and 26) gave (±)-O-methylthalisopavine (4) and (±)-argemonine (5), respectively.